Tim's Journey Ch. 08

Story Info
Connie meets the best man.
4.8k words
4.39
50.1k
15
3

Part 8 of the 8 part series

Updated 09/25/2022
Created 06/15/2005
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
goamz86
goamz86
1,996 Followers

Letter from the author: This story deals with female domination, humiliation and a less than confident man. He lives to please his woman, and it turns him on to see her with other men. If you don't like this kind of story, please move on. For those of you who do enjoy that, please enjoy and feel free to comment and/or e-mail me with comments. I love to hear if the readers like my work. I don't mind criticism if it is constructive.

Thank you for reading,

Goamsz86

*

It was three weeks after the bachelorette party. Tim and Connie were busy preparing for the wedding that was now 4 days away. Connie had been good, keeping her promise, saving her pussy for Tim's one venture into it on their wedding night. However, she needed some cock and she needed it soon.

Tim had to go pick up the best man at the airport. His best man was his lifelong friend Raymond. They had been friends since the first grade in Mrs. Green's class. They attended school together until they graduated from high school. Ray had attended college after high school and had moved away for a job opportunity. The two of them had always kept in touch regularly via e-mail. They had made a promise to be best man at each other's wedding. So when Tim called Ray to tell him he was getting married, Ray immediately made reservations to attend.

Connie had heard Tim speak often of Ray, but had not had the pleasure of meeting him yet. She looked forward to it. Connie did not enjoy meeting Tim's family, as they were very judgmental about her age. She hoped this would be different and she could be close to someone important in Tim's life.

Tim picked up Ray from the Airport and took him to meet Connie at her work. They walked in the office and Sarah told him to go on in. Sarah turned and watched the hunk of a man walk into Connie's office, noticing the fine firm ass in his business slacks. Connie's reaction was no different. When they entered her office she looked up and her jaw dropped. Ray was a vision, tall, dark and handsome. His body was magnificent in his clothes; she could only image what it looked like out of them. His facial features were striking, especially his eyes. Connie was not sure she could stand up to meet him, as her knees felt weak.

"Well hello Raymond." She said as she gathered enough strength to stand and approach them. "Tim has told me so much about you. It is a pleasure to finally meet you."

She extended her hand. "Get out of here." Ray scolded her. He wrapped his arms around her and gave her a great big hug. "Any woman that makes Tim as happy as he says you make him gets a hug from me."

Connie's whole body melted in his arms. His strong grasp was overwhelming. She wanted him to take her right there in her office, bend her over the desk and fuck her like a bitch in heat. She reached around his strong firm body and hugged him back. Her cheek rested against his chest and she inhaled his scent. It was intoxicating. When the embrace broke they both backed up but still held each other's hands.

"You didn't tell me he was so handsome Tim." Connie said.

"Yea, yea, yea." Tim replied, flippantly. "All the girls say that."

"All the girls are right dear." She said curtly.

She stood back still holding on to both of Ray's hands and took in the sight of him once more. Ray did the same. He could see why Tim liked Connie. He knew Tim's tastes, and she was everything he knew Tim liked. Ray could not take his eyes off her massive tits. Her top had a low neckline and he just drank in the sight of her cleavage. His cock stirred in his pants and he realized he was staring at his best friend's fiancé. He recoiled his hands and told himself to stop looking at her that way. However, they both could feel the attraction.

"It's almost lunchtime. You boys hungry?" Connie asked.

They both looked at each other and said, "Sure."

Connie turned and retrieved her purse from the desk drawer and the three of them headed out to lunch. When they got to the restaurant Connie suggested they have a drink to celebrate Ray's arrival. One drink turned into three or four and soon they were all laughing and having a great time. Connie listened as Ray and Tim told her story after story about their childhood. They all ordered their meals and ate. After that the drinks continued and soon it was almost 4PM.

As she got more drinks in her, Connie got bolder. She began to ask Ray to tell her about Tim's sex life in high school. Ray joked that he wasn't sure if Tim had a sex life in high school. Connie laughed out loud and then she placed her hand on Ray's thigh out of Tim's sight. She moved it up toward his crotch.

"I'll bet you had an active sex life in high school huh?" She said, as her hand inched closer to his crotch.

Ray got a bit uncomfortable. He looked at Tim and noticed he was oblivious to what was happening. He never could hold his liquor too well. He looked down at Connie and all he could see was her fuck me eyes and her massive amounts of cleavage staring him right in the face. He was feeling good, but this was his best friend's fiancé. He couldn't do this. Just about that that time, Connie's hand reached his growing cock. She began to massage it through his pants and it grew to complete firmness.

Connie was impressed by its size. She moved her hand up and down its length. Ray didn't know what to do. He didn't want to cause a scene, but he knew this was wrong. How could this bitch do this to his best friend, especially right in front of him? He wanted to move, but she was really good with her hand and it felt good. Before he knew it, she had his pants unzipped and her hand was inside them and she was stroking his now throbbing cock. It wasn't like he could get up now, how would he explain his pants being open and his cock rock hard. He tried to slyly put his hand on her wrist and pull it out.

Connie only grabbed harder and stroked faster. Feeling Ray's cock grow stiffer, she looked at Tim, "Honey, why don't you call Sarah and have her come pick us up and take us home. We have all had a little too much to drink."

Tim grabbed his cell phone and began to dial.

"Sweetie," She said, still massaging Ray's manhood. "Don't be rude; go call her from the lobby. People don't want to hear your phone conversation while they eat."

Tim got up and stumbled to the lobby to call. As soon as he was out of sight, Ray pulled Connie's hand from his pants.

"What the hell are you doing?" He said sternly.

Connie swiftly put her hand right back in his pants.

"What do you think I'm doing? I'm playing with your cock, and by the feel of it, you are enjoying it." She said quietly into his ear.

"Stop it!" He snapped. "You are my best friend's fiancé. You are getting married on Saturday." He pulled her hand from his pants, zipped his pants up and scooted out of the booth. "I'm going to the bathroom."

Connie sat up in the booth and soon Tim returned.

"Sarah will be here in about a half hour. She is waiting for the UPS guy to come." He informed her.

Connie scooted out of the booth, kissed Tim on the cheek and told him she needed to use the restroom. Tim smiled and watched as Connie's wide ass jiggled in her skirt as she walked away. He could hardly wait to fuck her on Saturday night.

Ray stood at the urinal trying to pee. His cock was rock hard and he could not get it to release his urine. No one was around, and he knew the only way he could get it to go soft, was if he stroked it and got it off. He was blocked from the door, so if anyone came in, he could stop before they saw him. He grabbed hold of it and began stroking it quickly as to get it over before anyone caught him. He closed his eyes and recalled Connie's huge sweater puppies. It felt good, and he would soon be blowing his wad. His balls began to ride up and he could feel his orgasm looming. He stroked a bit harder and faster. Man, what it would be like to see those things in the nude. He was almost there.

"Would you like some help with that?"

Ray froze. "Oh shit!" He gasped. He turned and there was Connie. She had slipped in the bathroom so quietly, that he hadn't even heard her.

Connie couldn't believe her luck. Not even her dirty little mind could have imagined she would find this. She was just hoping to corner him in the restroom and try to seduce him. She knew he would be an easy target now. She got on her knees and looked up at him.

"Let me finish what you started." She said.

With Connie and her cleavage staring at him and a throbbing cock in his hand, Ray's resistance was gone. He turned and presented his rigid manhood to Connie. She reached out and grabbed it, stroking it slowly as Ray moved closer to her. When it neared her face, she opened her mouth and guided it all the way to the back of her throat. Ray moaned as her hot mouth engulfed it. He watched as Connie began to bob her head back and forth, sucking deeply each time it pulled from her mouth.

Connie also moaned as the thick hard cock in her mouth moved past her lips and found the back of her throat. She was so aroused. She had not seen a cock in more than three weeks, let alone feel one in her hand or mouth. Soon she was sucking for all she was worth. Faster and faster she moved, stroking with her hand as well as sucking it with her mouth. Ray was getting lightheaded. He grabbed onto Connie's head for support. He noticed that this seemed to turn her on as she began to look up at him and moan louder. He began to be a bit more forceful, pulling her head into him a bit harder. Connie reached around him and grabbed hold of his ass to help. Suddenly she wasn't sucking his dick as much as he was fucking her face.

Ray's rhythm was at a fever pitch as his cock impaled Connie's face. His balls tightened and his orgasm bolted to the surface. Ray pulled Connie's face in hard and held it there with her nose buried in his pubes. His cock exploded down her throat like a rocket. He pulled his cock almost all the way out then back deep into her throat as it erupted again. Connie just sucked down both bursts of his hot thick love juice. Ray pulled her off his cock again and then with three of four more quick strokes he emptied the rest of his load down Connie's throat. His knees became week and he almost collapsed on the floor. He stumbled back and his cock popped from Connie's lips. He fell against the wall and regained his balance.

"That was incredible." Ray told her.

Connie got up and approached him. She grabbed his withering cock and kissed him on the lips. "There's more where that came from lover." She quipped. "See you back at the table." She turned and walked out of the bathroom. She passed a gentleman standing outside the door. He had a surprised look on his face. She knew he had caught them, but she didn't care. She looked him square in the face and winked as she walked by.

Ray stood leaning against the wall recovering and trying to reconcile in his mind what he had just done with the fiancé of his dearest friend in the whole world. He felt like a complete ass. How could he face Tim? He pulled up his pants and someone entered the bathroom. He tried to hide his face, but the guy gave him a knowing grin. He went to the sink and stared into the mirror. He was horrified at the image looking back at him. He just stood there as the other customer finished his duties and came to the sink. Ray just hung his head thinking the guy was judging him. The other guy washed his hands and left. Ray just stayed there trying to get the nerve up to face his friend.

When Connie returned to the table, Tim had dozed off, an effect of the alcohol. Connie slid into the booth and Tim was startled back to consciousness. Connie leaned over and kissed him on the cheek.

Tim's head was still a bit fuzzy when Sarah arrived to take them all home. Connie told Tim to go find Ray.

"Hey Ray, you fall in or something?" Tim called out as he entered the restroom.

Ray turned to look at Tim as he came face to face with his friend.

"No, just not feeling the best, must be the alcohol or something." He replied as the two turned and exited the room.

The four of them piled in the car and Connie worked it so Tim was in the front and Ray was in the back with her. She teased him the whole way home. Ray tried his best to ignore her, but she fondled her tits and pulled her skirt way up, even turning to flash him a view of the silky red panties she was sporting. Ray's cock responded, but he kept as much distance between them as the back seat would allow.

Connie was relentless the rest of the evening, as the four of them had dinner at home and enjoyed each other's company until bed time. Every chance Connie got when Tim was not looking, she made advances toward Ray. He didn't know what to do. If he told Tim he might lose his friend, but he thought his friend needed to know what a slut he was marrying. On the other hand, he really wanted to fuck this nasty bitch in the worst way. He would wrestle with these two for the next four days. Little did he know what kind of relationship Connie and Tim had.

That night when Connie went to bed, she invited Tim to come with her. This of course thrilled him. He knelt on the floor at the side of the bed and waited for Connie as she was in the bathroom preparing for bed. She entered wearing a long, black, silk robe tied loosely in the front. She approached him, opened the robe and dropped it to the floor. Connie wore nothing but the same pair of silky red panties she had been flashing to Ray. Tim could see they were already wet. He breathed in deeply smelling her arousal.

"Take off my panties my pet." Connie ordered. "Clean them."

Tim knew what that meant. He pulled them down over her broad hips and round ass. Connie stepped out of them and Tim turned them inside out and began cleaning the soiled crotch with his tongue. The taste of her arousal was enthralling for Tim. His already hard cock throbbed even more now. He sucked and licked every bit of her taste from the undergarment. As he did that, Connie began to tease him and humiliate him.

"You know what got me so turned on tonight?" she asked.

Tim shook his head.

"The taste of your friend's cum." She answered.

Tim looked at her with a puzzled look.

"That's right; I sucked his cock this afternoon in the restroom at the restaurant." She told him.

Tim was jealous, enraged and turned on all at the same time.

"Does that turn you on?" she asked.

Tim nodded.

Connie got on the bed, spread her legs wide, and spoke, "Come eat my pussy and momma will tell you all about it."

Tim scurried onto the bed and buried his face in her steaming snatch. He eagerly devoured her pussy as she recalled the afternoon rendezvous.

"He has such a nice big cock my pet, not like that pathetic little penis you have. He was in the bathroom stroking it when I snuck up on him. I offered to finish what he started. He let me suck his big fat cock into my mouth." She told him as she grabbed Tim's head and pressed it into her pussy.

Tim licked and sucked and nibbled on her juicy cunt as Connie continued, "His cock slid all the way in until it hit the back of my throat. Your pitiful little penis could never do that." She scolded him.

This only spurred on his pace.

"That's it sweetie, suck momma's clit make me come." She instructed.

"Your friend is a real man. He fucked my face like I was a common whore. He made me feel like a woman, unlike you my wimpy little pet." She again admonished him.

Tim looked up and saw Connie pinching and tweaking her nipples.

Her voice got higher and her breathing became shallow as her orgasm surfaced. Tim recognized the signs and inserted three fingers into her pussy and nibbled hard on her clit. "Then he forced his cock down my throat and.....and.....and...." her orgasm hit and her body shook as she finished her sentence, "He....He.....He emptied his load of sweet hot cum down my throat!!!!!!!"

Her body convulsed and shook as her orgasm rushed through her. Tim continued his duties the whole time until Connie's whole body went limp and she pushed him from her pussy. Tim rose to his knees and Connie could see his little pecker standing at attention. It jumped with each pump of his heart it was so hard. She looked at him and told him he could go take care of himself in the toilet. Tim raced to the bathroom as Connie covered herself and dozed off to thoughts of Ray's cock.

After Tim had relieved himself into the toilet, he returned to Connie's room. He stared at her, dreaming of what it was going to be like to actually get to fuck Connie on Saturday night. He crawled up on the bed and curled up under a blanket at the foot of the bed. Ray was using Tim's room while he stayed there.

*********

For the next three days, Connie tried in vain to seduce Ray. She walked around the house half naked. She cornered him several times. She even attempted it at the rehearsal dinner while Tim's whole family was just around the corner. However, no matter how much she tried to explain that Tim couldn't satisfy her as a woman, Ray would just not give in. Connie didn't want Ray to know she fucked other men with Tim's knowledge. She knew it would be more taboo in Ray's head if she could seduce him without Tim knowing, and therefore be more exciting to him. This always made for better sex in her mind. When the wedding day came around, she was becoming desperate. Ray would be gone today and she had to have his cock in her or she would just die. Tim was sleeping in Sarah's room the night before the wedding and was told to get up early and leave as not to see the bride on their wedding day. Connie woke up and tried one more time that morning by sneaking into Ray's room. He woke up with his cock in her mouth. He reluctantly had escaped and was now with Tim at the church waiting for the ceremony that was to start in about 30 minutes.

*******

Connie and the bride's maids had all arrived about an hour ago after a visit to the salon for manicures, pedicures, make-up and hair styling. Ray had caught a glimpse of all them as they shuffled by to the Bride's room where they would all get dressed. Connie was wearing just a t-shirt and a pair of terrycloth shorts. She was not really Ray's type (too fat), but even dressed like that, she looked stunning. Her face glowed, and suddenly he regretted not taking her up on her numerous offers to fuck her. He gazed at her as she walked by, and Connie knew what he was thinking. She too was feeling that a great opportunity had passed them by.

All the girls had helped Connie dress first, and were shuffled off to another room to finish preparing, leaving Connie ready with more than 30 minutes to the ceremony. She sat at the mirror taking it all in. She really did feel lucky. Tim was a wonderful man who worshipped the ground she walked on, and his understanding of her sexual needs made for a perfect arrangement. She just knew she would be happy. As she stared into the mirror in deep thought, there was a knock on the door.

"Come in." Connie called out.

The door opened and Ray peaked around it, "You decent?"

"Sure am, come in." she assured him. "How is Tim?" she inquired, as she stood and walked toward Ray.

"He is fine, a bit nervous, but fine." He answered.

There was an awkward silence. Connie now stood only a few inches form him. Ray was blown away by how good she looked. He couldn't believe he had not fucked her. He scoured his mind for the words he wanted to say. He opened his mouth to speak, but before he could get a sound out, Connie flared her dress as not to wrinkle it, dropped to her knees and lifted her veil. He watched as she unzipped his pants and pulled his growing cock from his pants. Without a word, she swallowed his entire length. She sucked his cock to hardness, being very careful not to mess her make-up. Her pussy began to tingle and her nipples stained against the tight material of her dress. She left copious amounts of saliva on his cock, knowing they would need the lubrication.

goamz86
goamz86
1,996 Followers
12